Multi-step reaction with 10 steps
1: ZnCl2 / tetrahydrofuran / -78 °C
2: 70 percent / 2,6-lutidine / CH2Cl2 / 0 °C
3: 1.) lithium hexamethyldisilazide, 2.) I2 / 1.) THF, -46 deg C to RT, 2.) THF, -46 deg C
4: tetrabutylammonium fluoride / tetrahydrofuran / -46 - 20 °C
5: 93 percent / H2 / Pd(OH)2 / methanol / 50 °C
6: HCOOH / Ambient temperature
7: (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, i-Pr2EtN / CH2Cl2 / 0 °C
8: NH3 / methanol / Ambient temperature
9: 2,6-lutidine / CH2Cl2 / Ambient temperature
10: 80 percent / t-BuLi / tetrahydrofuran / -78 °C
With
2,6-dimethylpyridine; formic acid; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonia; hydrogen; iodine; tert.-butyl lithium; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; lithium hexamethyldisilazane;
palladium dihydroxide;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0957-4166(99)00041-5